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(S)-fuscumol and (S)-fuscumol acetate produced by a male Astyleiopus variegatus (Coleoptera: Cerambycidae)

Published online by Cambridge University Press:  29 January 2013

Gabriel P. Hughes ,
Yunfan Zou ,
Jocelyn G. Millar  and
Matthew D. Ginzel
Gabriel P. Hughes
Affiliation:
Department of Entomology, Purdue University, West Lafayette, Indiana 47907, United States of America
Yunfan Zou
Affiliation:
Department of Entomology, University of California, Riverside, California 92521, United States of America
Jocelyn G. Millar
Affiliation:
Department of Entomology, University of California, Riverside, California 92521, United States of America
Matthew D. Ginzel*
Affiliation:
Department of Entomology, Purdue University, West Lafayette, Indiana 47907, United States of America
*
1Corresponding author (e-mail: [email protected]).
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Abstract

Within the family Cerambycidae (Coleoptera), (E)-6,10-dimethyl-5,9-undecadien-2-ol (fuscumol) and (E)-6,10-dimethyl-5,9-undecadien-2-yl acetate (fuscumol acetate) have been shown to attract several species in the subfamily Lamiinae. However, it is not yet clear whether beetles within the subfamily actually produce these compounds as pheromones or rather respond to them as kairomones. We report here that male Astyleiopus variegatus (Haldeman) produce both fuscumol and fuscumol acetate, suggesting that the compounds are indeed pheromones for this species. We also determined that the absolute configurations of these compounds are (S)-fuscumol and (S)-fuscumol acetate by synthesis of both enantiomers of each.

Résumé

Il est connu qu'au sein de la famille des Cerambycidae (Coleoptera), le (E)-6,10-diméthyl-5,9-undécadién-2-ol (fuscumol) et l'acétate de (E)-6,10-diméthyl-5,9-undécadién-2-yle (acétate de fuscumol) attirent plusieurs espèces de la sous-famille des Lamiinae. Il n'est cependant pas clair si les coléoptères de la sous-famille produisent de fait ces composés comme phéromones ou alors y réagissent comme à des kairomones. Nous rapportons ici que les mâles d’Astyleiopus variegatus (Haldeman) produisent à la fois du fuscumol et de l'acétate de fuscumol, ce qui laisse croire que les deux composés servent de phéromones chez cette espèce. Nous avons aussi déterminé que les configurations absolues de ces composés sont le (S)-fuscumol et l'acétate de (S)-fuscumol par la synthèse des deux énantiomères de chacun.

Type
Behaviour & Ecology – NOTE
Information
The Canadian Entomologist , Volume 145 , Issue 3 , June 2013 , pp. 327 - 332
Copyright
Copyright © Entomological Society of Canada 2013 

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References

Fonseca, M.G., Vidal, D.M., Zarbin, P.H.G. 2010. Male-produced sex pheromone of the cerambycid beetle Hedypathes betulinus: chemical identification and biological activity. Journal of Chemical Ecology, 36: 1132–1139.CrossRefGoogle ScholarPubMed
Graham, E.E., Mitchell, R.F., Reagel, P.F., Barbour, J.D., Millar, J.G., Hanks, L.M. 2010. Treating panel traps with flouropolymer enhances their efficiency in capturing cerambycid beetles. Journal of Economic Entomology, 103: 641–647.CrossRefGoogle Scholar
Hanks, L.M., Millar, J.G., Mongold-Diers, J.A., Wong, J.C.H., Meier, L.R., Reagel, P.F., et al. 2012. Using blends of cerambycid beetle pheromones and host plant volatiles to simultaneously attract a diversity of cerambycid species. Canadian Journal of Forest Research, 42: 1050–1059.CrossRefGoogle Scholar
Hanks, L.M., Millar, J.G., Moreira, J.A., Barbour, J.D., Lacey, E.S., McElfresh, J.S., et al. 2007. Using generic pheromone lures to expedite identification of aggregation pheromones for the cerambycid beetles Xylotrechus nauticus, Phymatodes lecontei, and Neoclytus modestus modestus. Journal of Chemical Ecology, 33: 889–907.CrossRefGoogle ScholarPubMed
Lingafelter, S.W. 2007. Illustrated key to the longhorned woodboring beetles of the eastern United States. The Coleopterists Society, North Potomac, Maryland, United States of America.Google Scholar
Millar, J.G., Hanks, L.M., Moreira, J.A., Lacey, E.S. 2009. Pheromone chemistry of cerambycid beetles. In Chemical ecology of wood-boring insects. Edited by K. Nakamuta and J. Millar. Forestry and Forest Products Research Institute, Ibaraki, Japan. Pp. 52–79.Google Scholar
Mitchell, R.F., Graham, E.E., Wong, J.C.H., Reagel, P.F., Striman, B.L., Hughes, G.P., et al. 2011. Fuscumol and fuscumol acetate are general attractants for many species of cerambycid beetles in the subfamily Lamiinae. Entomologia Experimentalis et Applicata, 141: 71–77.CrossRefGoogle Scholar
Pajares, J.A., Álvarez, G., Ibeas, F., Gallego, D., Hall, D.R., Farman, D.I. 2010. Identification and field activity of a male-produced aggregation pheromone in the pine sawyer beetle, Monochamus galloprovincialis. Journal of Chemical Ecology, 36: 570–583.CrossRefGoogle ScholarPubMed
Silk, P.J., Sweeney, J., Wu, J.P., Price, J., Gutowski, J.M., Kettela, E.G. 2007. Evidence for a male-produced pheromone in Tetropium fuscum (F.) and Tetropium cinnamopterum (Kirby) (Coleoptera: Cerambycidae). Naturwissenschaften, 94: 697–701.CrossRefGoogle ScholarPubMed
Sweeney, J.D., Silk, P.J., Gutowski, J.M., Wu, J., Lemay, M.A., Mayo, P.D., et al. 2010. Effect of chirality, release rate, and host volatiles on response of Tetropium fuscum (F.), Tetropium cinnamopterum Kirby, and Tetropium castaneum (L.) to the aggregation pheromone, fuscumol. Journal of Chemical Ecology, 36: 1309–1321.CrossRefGoogle Scholar
Teale, S.A., Wickham, J.D., Zhang, F., Su, J., Chen, Y., Xiao, W., et al. 2011. A male-produced aggregation pheromone of Monochamus alternatus (Coleoptera: Cerambycidae), a major vector of pine wood nematode. Journal of Economic Entomology, 104: 1592–1598.CrossRefGoogle Scholar
Vidal, D.M., Fonseca, M.G., Zarbin, P.H.G. 2010. Enantioselective synthesis and absolute configuration of the sex pheromone of Hedypathes betulinus (Coleoptera: Cerambycidae). Tetrahedron Letters, 51: 6704–6706.CrossRefGoogle Scholar
Yanega, D. 1996. Field guide to northeastern longhorned beetles (Coleoptera: Cerambycidae). Illinois Natural History Survey Manual 6. Illinois Natural History Survey, Urbana, Illinois, United States of America.Google Scholar